I'll Try To Do Better
by not the mermaid
Summary: Plot: Reader is shy, sick, and going through a lot of body and self esteem issues and Jesse just wants to help them get their life back on track and help them feel better. I wrote this (my 1st xReader) as a bit of a personal monologue a while ago so it's quite angsty and i wasn't even going to post it to my ao3 until i had a friend kinda push me towards putting myself out there


You and Jesse were watching tv in the living room, the two of you cuddled up together on the couch giggling in your tank tops and sweatpants having a lazy day. You were watching kitchen nightmares and he was joking about eating at much worse places. He relished in the sound of your contagious laughter as his playful hands trailed up your sides and beard both tickling you as he nuzzled into your neck. You were laughing so hard you instinctively started to cover your mouth. Jesse noticed this and frowned for a split second, he hated when you covered your face from him, it made him feel like you didn't want to show your expressions towards him even though deep down he knew that wasn't true. He pulled you closer into him and peppered a few kisses onto your neck and face, his kisses always made you smile. It was Saturday and the both of you had the day to yourselves so you guys decided to have a lazy day relaxing, catching up on tv and movies.

You cracked your back and rubbed your neck with a groan, you had chronic pain so your body was always under constant stress, today wasn't so bad for you but you were still feeling kinda stiff in your joints. You stood up to stretch a bit and every time you moved something involuntarily made a cracking sound. You could hear Jesse tut and stand up behind you, he picked you up bridal style and looked at you with concern "Darlin you're soundin like you were made outta bubble wrap. Why don't I take you in the bedroom to give you a massage and rub out all of those kinks?"

You blushed at his comparison but you couldn't deny it at all unfortunately, "Heh… ok Jess I'll take you up on your offer, not like i can really decline it anyways, you already carried me to our room" you teased

The cowboy smiled and gave u a kiss on top of your head before setting you down on the bed. "Alright sweet pea you know the deal". You sighed knowingly as you started to remove your pants and shirt before laying face down on the middle of your bed. Jesse frowned at you for keeping your bra on, that was another thing that you did all the time that made him upset, if you weren't trying to keep your bra on it seemed as tho you were trying to cover yourself with other things like your hands or pillows and blankets. You've seen each other beyond naked many times so he just didn't understand why you were always being so shy and trying to hide yourself from him all the time. He hoped he wasn't making you feel insecure somehow but he also didn't wanna upset you by addressing it. He took off his shirt and sighed as he climbed onto the bed with you and went over to unhook your bra "Honey you know you're supposed to take your bra off too why do you keep it on all the time?" he asked concerned in a soft voice.

You muffled a small "I'm sorry" from where you were laying and pulled the bra from underneath you before throwing it onto the ground.

The cowboy sighed again as he applied lotion to his calloused hands got to work on your neck and shoulders "it's alright sweetheart, just know you don't have to hide yourself from me ok?". You didn't answer but he saw you nod your head slightly. It always made him worry with concern when you hide yourself from him, he knew you were a little shy but after being together as long as you two have he would have thought you would feel more secure around him. He just tried to brush it off like he always did when these things happened and focus on making you feel better instead.

After getting all of the little knots and kinks out of your back and shoulders Jesse started to pepper you up with kisses again starting from the middle of your back to nipping at your neck, his beard tickling you the entire way up making you giggle so hard Jesse had to wrap his arm around you to keep you still. He didn't mind at all though because he was definitely doing that on purpose just to hear you laugh. You moved yourself over to face him and steal a few kisses which turned rougher and more heated than the playful kisses he was just giving you from just a few moments ago. Jesse began to smirk into the kiss as he let his hands start to roam from your back to your chest, teasing your nipples making you whimper into the kiss. Jesse broke the kiss and trailed down to your neck, nipping and biting your most sensitive areas. His hands played with the waistband of your panties before pulling them down and smacking your ass hard, cupping and squeezing your soft round cheeks. Your moans signaled to him that it was time to get a little more rough and you were ready for the main act. The cowboy left one last small departing kiss on your neck before getting up to take his sweats off.

As he got off you you took a pillow and held it to your chest as you sat up to see the show "Do you always go commando cowboy?" you smirked as you laid eyes on your prize.

McCree chuckled "As often as i can princess, you know that." he looked at the pillow you were using to cover yourself and frowned but didn't want to mention it, he didn't want to ruin the moment, instead he just asked you to lay down for him so he could get in position and moved the pillow away from you as he leaned down into you for another kiss before working on your body again. The cowboy spread your legs and lifted one to sit on his shoulder as he kissed down from your knee to your inner thigh. He moved his hand down to your destination and spread your lips with his middle finger, "Look at that, all nice and wet for me. Yer almost ready for me darlin but not quite yet" he grinned at you as he started rubbing your clit, making your body shudder and squirm. Jesse smirked at your body's reactions and the wanton look on your face pleased, he inserted two fingers and massaged your sweet spots, making you moan and whimper wanting more. "Thats its baby girl, i feel you getting close, just relax and let me handle everything. you're so perfect, just come i know you're so close baby you're almost there…" as Jesse spoke his praises to you in is smooth southern voice he started to move faster and faster, you started to feel more and more outta control, moans getting louder and louder so you instinctively grabbed a pillow from your side and covered yourself long ways so it covered both your chest and face at once. Jesse noticed this immediately and he just couldn't shake off you hiding from him anymore. No longer could he handle the thought of making you feel insecure or uncomfortable. Shyness was one thing but you guys have been a couple for years so there was no way that was still the case. Mccree took a deep breath and stopped pleasuring you and gently put your leg back down.

You looked up from your pillow at him and in a tired breathy voice you asked "Baby what's wrong, why did you stop?! I was was so close, i was ready f-" Jesse cut you off before you could even finish your sentence

"Darlin if you really were ready why are you hiding from me behind pillows? Am i hurting you? Am i doing something wrong?" he asked bluntly and he sounded pretty upset.

"I…" you were surprised to hear him so upset so you tried to pick your words carefully as you sat up against the headboard still clutching your pillow. "No baby you've never done anything wrong and you've never hurt me before." you looked up at him with sad eyes but tried to give a look of reassurance, "I….I guess I'm just….shy or… insecure about some things still….i know we've been together for a long time and you've seen me naked countless times but it just… i dunno…" you trailed off unsure of yourself, avoiding eye contact with your boyfriend standing in front of you.

McCree sighed, upset that his suspicions were right. He sat next to you on the bed and pulled you into him, laying his head on your shoulder, a serious yet sad aura radiating from him as he held you. "I'm sorry…"

You perked your head up confused at his apology, "Sorry? For what" you asked concerned and confused because he had nothing to apologize for.

"I'm sorry for not doing what any man should do and make sure all of your insecurities were washed away years ago, i should have asked this a long time ago so i knew how to help you get rid of them ages ago. I just figured you were just bein shy… for a while i thought it was cute but after so long i thought your shyness should have gone away, and i was right. So I'm sorry for not asking and stepping up sooner." he hugged you tighter and pulled you closer into his lap. "What is it that you're so insecure about darlin? I wanna know so i can start making you feel better about yourself as soon as possible" he asked in a determined voice.

"W...well...i….no it's dumb you're gonna think it's ridiculous" you shook your head and laid it against the pillow you were still clutching onto

"Darlin please, it don't matter to me how silly it is, because it's something that's affecting you and bringing my baby girl down. If it's somethin i can help fix i need to know"

You sighed knowing how ridiculous you were about to sound, but he wasn't going to let it go until you told him so you might as well tell him sooner than later. "I….i cover my face a lot during sex because i don't want to be too loud and think i look embarrassing…...and i cover myself all the time because I've been having a lot of body issues lately and i also just...i really don't like how my boobs look….." you painstakingly admitted through a pouting, frustrated face.

Jesse was confused but he was never judgemental, it wasn't his place to judge but rather to try and understand why you felt this way and try to make you feel better about these things. "I see… well sweet pea, you don't have to worry about bein loud while we make love now that we live in our own place. I want to hear you yell and scream! I love looking at your face and making eye contact with you during, it lets me know I'm doing a good job and that I'm not hurting you...in a bad way… and it's reassuring that the person i love is looking at me the same way I'm looking at them while we make love, it's such an important part of sex and every time you hide it makes me feel upset y'know…."

His words hit hard and made you slump down a bit as tears started to fill your eyes. You didn't realize how something as small as covering your face, to you, was such a big deal to him. "I...i'm sorry Jess…" your words shaky as you tried to choke back your sobs.

Jesse's heart fell into a pit in his stomach as he heard you crying and immediately turned you over to be facing him as he made you both slump down into the bed to lay back down. He held your face into his chest tight while petting your hair and rubbed your back in hopes that you would calm down. He never wanted to make you cry and now he's beating himself up over it.

"I'm sorry i never realized how something so small to me like covering and hiding my face and body would have such a big impact on you. I'm sorry for being so selfish, I'm sorry i-"

"Shhhh it's ok, i know you didn't realize, it's not your fault i should have asked these questions way sooner, don't be upset, we can work our way past these ok?" Jesse said in a small, caring, reassuring voice and gave you a kiss on top of your head while holding your hand and rubbing the back with his thumb.

You sniffled a few more times while calming down before looking up at Jesse with your big puffy tear stained eyes from his chest. He looked down at you and smiled before pressing a comforting kiss to your forehead.

"Hey sweet pea...while we're still on the topic, could ya explain what you meant by yer recent 'body issues' and also ya don't like yer own boobs? They're certainly not small or anything so why…?" he asked with both concern and confusion in his voice

You sighed and dug your head into his chest once more before taking a deep breath "Well, as you know, I've been losing a lot of weight involuntarily lately thanks to my pain causing me not want to eat and my depression about my whole situation lately just makes that way worse and now i feel like I've gotten way too skinny from it all and it's really just a vicious cycle of pain, mental health, and self image this point…." you sighed after getting off your chest and took a deep breath for what you were about to say next "as for my chest….to put it bluntly, they don't look like they even belong on my body." this made Jesse look down at you confused. "they're saggy with huge areola and every time i lay down without a bra, or when we have sex, it feels like they're trying to go into my armpit! Unless I'm on top riding you then of course they just want to flop everywhere. Quite frankly it feels like i have some gross udders on my chest rather than actual human boobs." you said with an angry pout on your face

Jesse tried his best to not laugh but that last sentence demanded a chuckle outta him. With a low whistle he scratched his head and looked back down at you "You feel real serious about this huh?". You just looked up at him with the pout still on your face but that was all the answer he needed "Well sugar, now i would never suggest goin underneath the knife for such cosmetic reasons, but i will say your breasts did feel bigger and more full when we first started dating. I reckon it's all the weight you've been losing that's made them less full. Now like ya said i know you haven't been losing all that weight purposefully and it's been a rough year with your health on the seemingly constant decline…" you sighed, trying not to cry again but it was hard whenever your health was the topic of discussion. He held you tight and lifted you up a bit so you would be face to face again since what he was about to say was important. "...i know you're not feeling good most days, and good days are far and few between lately but you do need to start taking care of yourself better. In fact I'm gonna help. I know you eat more and you eat healthier when people are around, and i know ya barely eat at all when you're alone so from now on we're eating every single meal together. Doesn't matter if I'm away on a mission or whatever, I'll video call you when I'm away if i have to!"

You looked at him like he was crazy, that was completely unrealistic with his job, but you knew he was crazy enough to do it.

"Jesse that's-"

"Nope! You can't refuse because you have no choice now. You need to start gainin your weight back and if this is what it takes then that's what we're gonna do! And once you start gettin ya weight back on ya and gettin some of your energy back you're coming to the gym with me 3 times a week at LEAST lil missy! Until then we can do somethin that'll be easier on yer body like yoga, i heard that kinda stuffs real good for people with a lot of pain n' stuff. Should help ya build better balance and get ya nice and toned too, the sooner you start liking how you look again the better. I'll ask Satya about it she seems to like it a lot! Also we gotta work on gettin ya a normal sleep schedule lil missy, sleeping anywhere between 4am-3pm is gonna stop startin tomorrow! It'll do ya good, ya don't realize how much sleep affects yer health but it does, plus actually bein up and doin stuff during the day time will make ya feel better emotionally too." Jesse started rambling happily of all the ways he wanted to start helping and suggesting all the ideas he had.

You stared him in the eyes surprised at everything he was saying but you couldn't help but smile, he was 100% sincere and really wanted you to get better and proving that he was willing to put in the time to do even the simplest, smallest things he could to start getting your life back on track. Things no one else would he was going to do it above and beyond for you. You couldn't help but start tearing up at how happy you were.

"Hey now…" he said in a low voice tutting as he wiped your tears away "what's wrong what did i say that upset ya? Was it the gym?"

"No Jesse it's just… I'm so happy i have you to help me…everyone's always suggesting things but no one ever actually seemed like they really wanted to help, and that's what i really need is someone to actively help me put my life back on track rather than telling me ideas you know…. I'm just...i..." your sobs got heavier but you tried to power through "i did try a lot to keep myself independent… but at some point the emotional toll and the physical toll just built up to be too much you know… Jess… i..." You tried your best to keep it together but all of your pent up emotions flooded out of you and you couldn't help but cry. You couldn't get any more words out so you just clinged onto the cowboy as tight as you could as you sobbed into his chest.

Jesse smiled and hugged back tight glad that he could finally help his girl now that he knew all of the things that were bugging her for only she knows how long. "There there sweet pea it's ok, i know you've been fightin this for a real long time now, i don't blame ya at all for not bein able to fight anymore at all. But darlin if it's one thing I've learned in all my years it's that independence doesn't mean doing every single thing by yourself with no help from others, that's insane and it's a shame that we grow up thinkin that. Independence means you have the confidence to be an adult and get help when you need it be it from your friends, family, that you've built yourself to have. But you need to surround yourself with loving reliable people, not ones who will just give ya a tip and be on their own way. And it seems that that's what happend to you darlin, so it would be my pleasure to help you back on your feet and invite you to my personal community of friends and family since it really seems like you need it. I'm just so terribly sorry for not doin this for ya sooner sweet pea, i didn't realize how blind i was to all the things botherin ya, but i promise to do better from now on and ask questions immediately when i suspect somethings up that you may be too shy to tell me yerself ok?" Jesse tried to calm you down as he spoke softly by rubbing your back and holding your hand, brushing his thumb on the back of it. By the time he had stopped speaking you had stopped crying and just laid there on his chest as you listened to him speak his personal words of wisdom. They actually made you feel a lot better, even though it did make you realize you probably did need some better friends. Since you were considered a civilian you've only met a few of Jesse's friends and family members but now it seemed like he was going to try and introduce you to everyone he held close to him. It warmed your heart at how much he was willing to do for you and you had no idea how you could possibly repay him for his kindness.

You looked up at Jesse with your red and puffy tear stained eyes as you scooched up to get closer to his handsome face, "i love you so much Jesse" you exclaimed before stealing a searing hot kiss from him

He smiled into the kiss as he pulled you in closer and squeeze you tighter, "i love you too darlin". He couldn't help but feel warmth and joy as he held you in your kiss, thinking about what he was gonna start helping you with first and which of his friends you should meet next. But he knew exactly when he could start helping you with your shyness in bed with a little trick he had up his sleeve he was more than excited to try later tonight.

[Bonus sex scene]

"Darlin tonight we're gonna help you face your shyness in bed and i can finally see that pretty lil face of yours get overcome in passion" McCree said with a devilish smirk on his face as you sat on the bed naked while he grabbed something from his closet.

"I'll try my best not to cover my face or anything else baby i promise!" you said concerned with what he was about to take out of that closet.

"Oh sweet pea you won't have to promise, not when i got this!" he took out a silk red tie from his closet and walked over towards you.

"A….tie? How is a- oh no" you grimaced at what was going to happen but you also couldn't lie that part of you was pretty excited to see how this would go. And since you were both still naked you could see your cowboy was pretty excited too

"Lay down princess" he commanded in a soft voice. You obliged and lie down in the middle of the bed. "Arms up above your head". You obeyed again, you loved when Jesse turned into your dom it brought out such a sexy side of him. He stood over you with the tie and grabbed both of your hands, kissing both of your wrists before tying your wrists together above your head. "There, now we don't have to worry about you hidin that pretty lil face of yours".

He climbed onto the bed and moved in between your legs "now where were we before…" he took your leg and placed it on his shoulder, kissing down from your knee to your inner thigh then up your abdomen to your chest, sucking and nipping at your left nipple, pinching and rolling the right one between his calloused fingers. He made his way up to your neck, nipping and biting at your most sensitive areas while his beard gave a wonderful tickling sensation. His skilled fingers trailing down your body until they reached your destination, spreading your lips and circling your clit with his rough fingers. Your moans and whimpers was like music to him, he left one final hot searing kiss on your neck to finally look up and see your face. Desperation and lust written all over it, you looked into his eyes craving more than what he was giving you. It was such a turn on to finally see you like this without blankets and pillows covering you he was so tempted to take you then and there but he restrained himself, he licked his fingers to get a quick taste before inserting his middle and ring fingers into you to massage your sweet spots. This caused you to squirm and moan even louder, you couldn't hold back he knew your body too well you were gonna cum for the first time tonight at any second and Jesse couldn't be more pleased.

"J-Jess…! Jesse! Please i-i'm…. I'm gonna...aaaah!" You couldn't hold back at all and came as his fingers rode out that first orgasm for you. You were breathing heavy and tears were in the corners of your eyes and you knew this was only the beginning of the night

"Ohhh look at that, look how adorable my baby girl is when she's in intense pleasure like that. I don't understand why you would wanna hide such a pretty face from me darlin especially when I'm the one causin all the pleasure." he licked his fingers clean before going to wipe the tears in the corners of your eyes away "Now i wasn't planning on eating my dessert tonight but darlin you just taste too good for me not to, and i wanna see how intense that O face can get with a lil overstimulation~" he chuckled devilishly before planting a kiss on your lips and working his way down.

"B-babe please you don't have to- i can't even return the favor tied up like this…!" you said trying to make an excuse out to prevent what you knew was coming next

Jesse chuckled as he put your legs around his neck "Your little excuses are too cute darlin, we both know i don't expect any 'favors' to be returned, if i do something it's because i want to and i like to do it. Now just lay back and relax, bon appetit " before you could protest again he was already eating his dessert. He started with a long slow lick separating your lips, testing the waters before he got to the clit, he gave it a few flicks before getting rough and sucking on it. The entire time he was trying to look at you and keep eye contact but you squirm around so much he was mostly just watching you moan and whimper, not that he has any problems with that either. He stuck a finger in your pussy which made you jolt up and crave more. You started to ride his face in desperation to be filled more, looking down at him with eyes full of lust, you couldn't even hold onto his hair because of the stupid tie. Jesse took the hint (after a little teasing) and stuck another finger in to help you with your orgasm. Jesse wanted to see how you handled a little bit of over stimulation so he kept massaging your gspot and refused to let your clit have a break for an extra few minutes which led to you sobbing in pleasure and your body trembling and being extremely sensitive.

Jesse wiped his mouth and hand off and took you in his arms "There there sugar it's ok shhhh" he said in a soft comforting voice as he wiped your tears and untied your wrists "you did so well sweetheart I'm so proud of you. We can take a quick break for now and then we'll finish up and go to sleep ok?". You nodded and nuzzled into his chest and rubbed your now red wrists. He took your hands once again and kissed the reddest areas from where the tie dug into your skin the most. You laid there cuddled up for a good fifthteen minutes before he said the break was over and tied your wrists back above your head. It was just enough time for you to stop trembling and shaking but definitely not enough time to stop feeling so extremely sensitive so you could only wonder how long you were gonna last. McCree hasn't had any type of release so far so even though he could usually last a very long time you were actually hoping this would go fast, for your pussy's sake.

The cowboy got back in between your legs, stroking his dripping length as you laid there both excited to finally have him fill you up tonight and nervous for how long this would last and how swollen your pussy was gonna be tomorrow. Jesse lowered himself, rubbing his tip between your lips. You smirked excitedly in anticipation. He could be such a tease sometimes but it was always worth it. He entered the tip into your aching hole and as slow as he possibly could sheath himself inside of you until both of your hips were touching. He bent down and gave you a kiss "nothing like some good ol vanilla missionary to see the woman I love as she gets pleasured the way she should right sweet pea?" You moaned as you shook your head and rolled your hips, adjusting to his girthy size and trying to get some friction going. He chuckled and took the hint as he started a slow rhythm pumping in and out, making sure to hit your sweet spot. You moaned in pleasure, his stroke felt so good you couldn't help the grin on your face, it was perfect for your overly stimulated pussy without feeling like it was bruising. But of course it couldn't have lasted for long, Jesse thought the look on your face as he warmed up was so adorable but that wasn't going to stop him from picking up the pace. The face you made as he started going faster almost made him stop because he thought he hurt you, that is until he heard the moans that you made with it.

"Jess….Jesse a...ahhh J-jess…."

"Yes Darlin?" he bent lower so he could hear you better and place a few kisses on your face

"f..fa-AH-faster! Deeper, please Jesse ahhhh" you tried to say between moans

Jesse looked at you surprised, he was trying not to hurt you since he's been pleasuring you all night he assumed you must be sore but hey if he had to carry you around all day tomorrow so be it. He lifted your legs onto his shoulders so he could get a deeper stroke going. The cowboy knew he was hitting the right spots by how tight you were squeezing him and how outta control your moans were getting.

"J-Jess! Jesse! Right there! Please! Right- ahh-"

"I got you baby girl it's ok its ok I'm right here you're doing so well baby just a little more ok you're so perfect i love you so much" he peppered your face in kisses and held you close as he rode out your orgasm. Your legs fell to his sides and were shaking,you knew he was close too because his strokes became more erratic and he was cursing under his breath. You felt him twitch inside you until his warm seed filled you up as he slowly pulled out exhausted. The cowboy sat up and untied your hands, kissing them and apologizing "I'm sorry i had to tie you up baby girl but it was worth it to see the cutest faces i ever did see you make". You blushed as he said that, still a bit embarrassed and self conscious about being so free like this in front of him. He spread your shaky legs to see himself dribble out of your used and swollen pussy, a devilish smirk appeared on his face "I'd carry you around everywhere everyday if this were my prize at the end of each day" he said with a sinister chuckle.

You rolled your eyes and pulled him back down to you to kiss his stupid face one last time before rolling on top of him and laying down on his chest. "We'll see about that" you say with a yawn before drifting off to sleep, you weren't even going to bother trying to stay awake after the way he just used you. Jesse chuckled as he watched you doze off on top of him, he carefully pulled the blanket that was falling off the edge of the bed on top of the both of you before closing his eyes and happily drifting off as well.


End file.
